Becoming Jessica Pt. 02


So we were ready to hit the piano bar. Or at least Emma thought I was ready. My first night out fully dressed as a woman, as Jessica. I was nervous and excited. I was also feeling unbelievably sexy and aroused. I felt so right sitting in the passenger seat of wife’s Land Rover as we made our way to the Marriott 5 miles away.

During the early part of the drive, and to break the initial silence, Emma said with a slight chuckle “My mother was right about you.”

“What?” I replied.

“She always thought there was something different about you. She said you were more like a friend to me rather than a husband. Guess it was your taste and interest in women’s clothing or something.” Emma explained.

“Yeah, or something.” I answered back.

Emma continued “Guess I just couldn’t accept it. It all makes sense now. But I’m glad you came out now rather years from now after having kids. That was really brave of you.”

“I had to Em. I hope we can help each other through this.” I said with a slight tone of seriousness.

“Of course silly. Why do you think we got all dressed up tonight? I’m looking forward to moving on, but helping you at the same time.” Emma replied.

I replied with a big smile and said “Thanks Emma, that means a lot.”

During the remainder of the drive Emma and I talked girl talk and listened to Beyonce. We discussed topics like who is hotter than who on The Bachelor and what we should dress up as for Halloween next month.

I didn’t really ever watch The Bachelor much so I just went along with the conversation. But Emma caught me up on the season and I was intrigued to watch it next week.

As for Halloween Emma always planned our costumes well in advance. “We should go out as sexy maids or nurses.” Emma shouted out.

I replied “Umm.That’s too common. How about flight attendants from that TV show Pan Am.”

I was always so envious of flight attendants and their cute uniforms.

“We could sexy it up with some cleavage, sky high heels, slits, and backseam stockings.” I added.

Emma replied “Now we are talking. I like it! Hot flight attendants. Sexy skirts with revealing slits.”

Emma and I gave each other a girly fist bump and agreed on our Halloween plans.

“I also would love to go out as Madonna in her bride costume from ‘Like a Virgin’. The whole ‘boy toy’ outfit with the bustier is so sexy.” I said.

“Wow you always hated Halloween as a guy Jess. I’m liking your train of thought. There is always more than 1 night of Halloween dress up fun. I can go as Britney Spears or something.” Emma giggled.

Along the way we stopped at a few stoplights. At one stop a car full of rowdy guys started hooting and hollering at us.

One of the guys even tried to get me to roll down my window and said “Come on babe! Where are you guys going tonight?”

Emma started to laugh.

I just politely smiled and winked at him as the light turned green.

Emma giggled and asked “Were you flirting with him? He was kind of cute.”

I replied “Nah. Not really my type.”

Emma quipped “Oh so Jessica has a type already? Oh la la. Do tell girl.”

I shyly replied “I like the muscular type, you know with nice arms and a chiseled chest, oh and have sexy eyes and a cute butt”. Guys like Josh Duhamel, Hugh Jackman, Tom Brady. They are my type.”

“No Jessica. I mean what do you want in a guy? Like his character and stuff. We all want guys like Josh, Hugh, and Tom Brady.” Emma added with a little giggle. .

I replied “Oh geez Em, I don’t know, I guess he has to be funny, interesting, masculine, athletic, like sports and dogs, have a good job, and know how to treat a woman like a lady, open my door, buy me flowers, sweep me off my feet, and put me on a pedestal and stuff.”

“That’s what I mean. I can’t argue with your taste in men Jess.” Emma said with a big smile.

As we pulled into the Marriott parking lot we were both surprised how busy it was as it was almost 11 PM.

On the Marriott marquee the sign read “Welcome TRUAD Group & Partners.”

Emma said they were a national pharmaceutical company and were in town for a convention.

Emma drove toward the valet and said with a wry smile “Guess we won’t be alone in there”.

She then took her wedding ring off and put it inside her purse.

She added “Remember we’re just a couple of girlfriends out for a drink. Some harmless flirting won’t harm anyone.”

As we waited for the car ahead of us to pull up I started to become very nervous and knew once I stepped out of the car there was no going back.

“Just remember the movements we practiced Jess. Wrists out. Tummy in. Chest out. Shoulders back. Feet and knees together. You’ll be fine girl. You already have the sexy walk in heels down.” Emma said.

As we reached the valet a young man opened my door, held out his hand, and helped me to my feet. I replied with a soft “Why thank you.” He then went around to help Emma. He didn’t seem to even bat an eye at me although Emma said anime porno with a smirk he couldn’t take his eye off my girls. It was a lovely moment to be helped to my feet by a man. I liked it and wanted more.

As we reached the front doors another young man working at the hotel opened the door and greeted us with a warm smile and said “welcome ladies”. I responded with a slightly pursed smile and said “Thank you so much” in a feminine tone.

Emma told me my voice and mannerisms were good so far. “No worries Jess. This will be fun.” Emma assured me.

We walked through the lobby and the sounds of our heels clicking attracted the glances of the front desk workers and a few patrons. No one seemed to notice anything peculiar. My confidence was growing as it seemed no one had clocked me. If anything I think Emma and I were attracting admiring glances from both men and women. We looked like a couple of young, attractive girlfriends going out on a Friday night.

As we headed toward the piano bar we passed the large convention center which was brimming with action. Men and women dressed to the nines were congregating around the main ballroom.

The convention schedule read “TRUAD Charity Ball”.

Most of the women were wearing full length gowns with beautiful jewelry and accompanied by sharply dressed men in tuxedos or 3 piece suits.

As Emma and I people watched in the convention lobby she joked “We look like a couple cheap gold diggers on the prowl for Mr Goodbar.”

I started to laugh pretty loudly which caught the attention of the convention goers.

Emma then got a call on her mobile phone. We scurried over to a comfy couch to sit down and blend in.

I remembered to sit lady like with my dress smoothed down, legs crossed, and purse placed on my lap.

One of the men in the convention area caught my eye. He was tall with dark brown hair and an athletic build. He had just loosened his bowtie with his strong looking hands when he glanced at me and smiled.

Emma nudged me and said “That guy is hot!” as she talked to someone named Kirk.

I quietly agreed and giggled. I couldn’t help but notice his broad shoulders and chiseled jaw and face. He looked my way again but I shyly looked away just in time as to not give away the fact I was checking him out.


Emma got off her phone and said “Great. We have a couple seats waiting for us at the bar. I know the bartender. He’s an old boyfriend.”

As we got up and walked out of the convention area Emma pointed to the marquee and said “Look they have two weddings planned for tomorrow night. We should crash a wedding here one of these weekends this fall and go as two single girls.”

The movie “Wedding Crashers” was one of our favorites and we always half joked about going as a couple and crashing a wedding one day.

But the thought of going as a couple of girlfriends dressed as wedding guests made me smile and say “Oh yes! I’m totally up for that!”

As we were about to leave the convention lobby and get on the elevator the hot guy from the convention area came up from behind us and said “Leaving so soon?”

Emma turned around and said with a little laugh “Leaving? We just got here”.

I just smiled and glanced at him. I couldn’t take my eyes off his handsome face and piercing eyes. I then flirtatiously loosened my knee length overcoat to partially reveal my legs and cleavage.

Emma added, “We’re not with the convention. We’re just going to the piano bar on the top floor for a few drinks.”

He replied, “Great. My friends and I are heading there later. My name is Drake. Maybe I’ll see you up there.”

Emma replied, “Maybe” as we both lightly laughed and stepped into the elevator. As the door closed Drake gave me a little wink and a wave of his hand as he pulled out his mobile phone. I was blushing and Emma knew it.

On the way up Emma said “Oh la la I think Drake has the hots for you Jess.”

I replied “Oh geeze. I don’t know about that.”

“Oh trust me girl, I know these things” Emma quipped and added “That little thing you did with loosening your coat sure got his attention. He was definitely into you. If you bump into him later just act natural, you’ll be fine. And hopefully one of Drake’s friends is cute. I can be your wingman.”

Emma starting laughing so I playfully nudged her on the shoulder and said “Don’t get any funny ideas. I’m not ready to carry on with a guy just yet.”

Emma replied “Oh I’m just teasing. But a little flirting can’t hurt.”

I just smiled as a rush of femininity came over me on the thoughts of flirting with a man, especially someone like Drake. It sent a warming shiver throughout my entire body.

The elevator door opened to the top floor and we checked our coats in the coatroom. Emma suggested we visit the ladies room first to primp ourselves before going into the lounge. I was excited and curious as I have never been a ladies room.

I was amazed how clean and girly it was. I also loved anne porno they had little couches, a few tables, and a basket of girly items, perfume, breath mints, powder, etc. .

I touched up my lips and mascara and Emma undid a couple of buttons on her red blouse to reveal a hint of her lacy red bra and cleavage. After we both checked our stockings and hitched them up a bit we headed to the lounge.

The host greeted us by saying “Oh you must be the two. A gentleman by the name of Drake reserved a window table for you near the pianos.”

Emma politely declined and told the host to thank him for us and that we’d be sitting near the bar.

As we walked toward the bar I nudged Emma and said “Why did you say that?”

“Well there are rules for single girls you know. For starters never accept drinks or table invites from strangers. He could be a creep for all we know.” Emma explained.

I replied “Whatever.” and rolled my eyes.

Emma added “Besides you have to play hard to get Jess. Men love the chase.”

We found the two seats at the end of the bar Kirk the bartender held for us. I followed Emma’s lead and hitched up my dress up a bit to in order to sit down on the bar stool. I remembered reading in Elle earlier how men are attracted to confidence and one important way to show this off was sitting upright and astute, and most importantly don’t slouch.

It was a bit awkward at first but I managed to cross my legs after carefully smoothing my dress. I also pulled back my shoulders which forced my chest out.

Emma gave an approving nod and said “Nice job girl. Show off your goods”.

It was a strange but wonderful feeling. I was dressed up as a woman in a lounge and trying my best to attract the attention of men. I felt sexy as hell, and to be honest a bit horny. My encounter with Drake had my mind racing with naughty thoughts and feelings. I felt my girly parts starting to stir a bit as well.

We began to scan the room as we listened to soft piano music and watched a few couples dancing. The lounge was filled with well dressed professionals wearing everything from evening gowns and suits to designer jeans.

The lounge had a nice mahogany smell and a great view of the Chicago skyline.

A bartender came over to us and said “Welcome to The Top Hat. What can I get for you ladies?”

Emma replied “Hi Kirk! We’ll take 2 house Pinot Noirs. Oh and this is my work friend Jessica.”

Kirk then came around the bar and gave Emma a quick hug and kiss and then kissed me on the cheek. KIrk was around 30 and had short blonde hair.

“He’s cute Em. And rugged. He looks like he played football” I said as Kirk turned to get our glasses of wine.

“Yeah. I had a thing for 6 foot quarterbacks in college. We had some fun times together. But he likes to stray a bit. He’s a womanizer.” Emma replied

As we waited for our drinks, an older intoxicated man perched next to Emma and tried chatting her up. Emma said something to him. He laughed but seemed to get the hint and staggered off.

Emma explained “You don’t have to be rude if a guy you’re not attracted to hits on you. Just tell him you have a boyfriend or you’re not looking to meet someone right now.”

I replied “So what did you say to him?”

“I told him my boyfriend is the bartender and he gets really upset when guys hit on me.” Emma said with a smile and chuckle.

“Haha nice one Emma.” I replied.

After Kirk poured our wine he began to chat with Emma.

A lady sitting next to me wearing a nice pantsuit complimented me on my dress and heels.

I quietly replied “Thank you, you wouldn’t believe it but I got them from TJ Maxx.”

The woman added “Oh how I love the bargains there.”

After the music stopped briefly the woman held out her hand and introduced herself “My name is Amanda and this is my husband Daryl.”

She then nudged Daryl who was glued to the TV watching the Chicago Cubs game. “Oh I’m sorry, it’s in extra innings.” as he briefly took his eyes off the TV.

HIs eyes quickly fixated themselves onto my cleavage to which Amanda said “Oh do you ever stop?” and poked Daryl in the ribs.

Half apologizing Amanda quipped “He’s always a flirt.” I just smiled and introduced them to Emma after Kirk went to serve other patrons.

Emma and I watched as Amanda and Daryl headed to the dance floor. It was funny but Daryl only agreed to go because he could still see the TV from the dance floor.

I then started chatting with Emma while we sipped our wine. I told her it seemed she was being quite flirty with Kirk. .

Emma said “Rule number two make good with the bartenders, especially cute ones. They watch over your drinks and they may buy you one on the house later. Maybe even go home with one.” as she gave me a foxy wink.

After Amanda and Daryl returned Amanda said “I can’t believe two attractive girls like yourselves don’t have dates tonight.”

I replied “Emma and I are just out on a late girls night arap porno out after she found out her husband was cheating on her; [laughing] I think she’s out for revenge. She’s eyeing up the bartender. Oh and I’m waiting on a nice guy I met down near the convention center.”

“You go girls” Amanda said with a chuckle as she high fived us.

About 45 minutes passed and Emma and I were on a 2nd glass of wine. I glanced over to Drake’s table but it was empty. Perhaps he got word we turned down his offer to sit there. Perhaps he hooked up with another girl.

Emma could tell I was getting down and grabbed my hand to go dance as the piano player was starting to play “Great Balls of Fire”.

This immediately cheered me up. I had never tried to dance as a girl but it was something to take my mind off Drake.

We got to the dance floor and again I followed Emma’s lead and tried to emulate her moves. I never really liked dancing as a guy, but as a girl I felt so sexy and knew there were several men watching us. It was a lot of fun. I loved glancing down at my cleavage and nylon covered legs.

Amanda and Daryl joined us and we became the hit of the dance floor. One of Daryl’s friends also joined in and tried talking to me during the song. I think he asked me to dance but I just smiled and mouthed “Sorry hun I can’t hear you.” I think he got the hint and kept to himself. He was Okay looking, but not my type. Besides I was still hoping for my Mr Goodbar, Drake.

After dancing Emma and I went back to the ladies room to pee and freshen up. For the first time I went to bathroom as a lady. I sat down properly after I lowered my undies. I let my balls pop back out and pressed my dick down in order to pee. Emma was right about wearing your panties over your garter belt. It made for much easier relief time on the toilet.

After peeing I put my boy parts back in their place and pulled my thong up and tucked my penis back again. My lacy boy shorts followed and smoothed my crotch area. As I readjusted and pulled up my stockings I noticed one had a run on the back of my calf.

“How embarrassing” I said to myself. I remembered Emma packed away an extra pair of stockings in my purse. I retrieved the plastic baggie which contained a pair of tan stockings. The only problem was I could tell they were a different hue and not as sheer as the ones I was wearing.

“What’s the hold up Jess?” Emma called out from beyond my stall door.

“I tore one of my stockings.” I replied.

“So grab one of your spare ones and swap them out” Emma said with authority.

“But they don’t match Em.” I replied.

“Oops.” Emma said with a little giggle. “My bad, I gave you the wrong ones. Those are my work stockings I bet.”

Luckily the bathroom was brimming with a ton of chatter from other women so my little debacle went unnoticed.

Emma continued, “So swap both of them out, but keep the good pair of Wolfords. Those are pretty expensive.”

I removed both of my shimmery Wolford stockings. I threw away the torn one and kept the good one. I then put on the matte tan stockings which just had a plain top. They were a little bit shorter so I was just able to pull them up to my mid thigh and had to readjust my garter straps.

I stepped out of the stall and pranced in front of the full length mirror while checking out my legs.

“They look fine Jess. No one will notice. Your legs look good with anything. You seriously have some killer stems” Emma cheerfully said.

Emma was right. Even though these stockings were a little darker and not skimmery, my legs still looked good. I also noticed how high heels elongated my legs.

After touching up my makeup and a couple squirts of my perfume Emma and I relaxed on the comfy chairs. It was after midnight and we discussed having one more drink or heading home.

We decided on the former and strutted back in. Kirk the bartender had saved our seats and we ordered two vodka martinis when we sat back down.

As our drinks arrived Emma nudged me and pointed to the table Drake had reserved for us. Much to my dismay Drake and 3 or 4 of his friends were gathered around the table with a harem of women wearing slutty nightclub dresses.

To make matters worse Drake lead one hussy to the dance floor during a slower piano ballad. Amanda and Daryl joined the floor as well.

Emma was wrapped up talking to Kirk so I hopped over to Daryl’s friend and playfully stomped my foot while saying “So, you were asking?” and gave him a flirty smile.

Chris or Rick [can’t remember his name] led me to the dance floor. He took the lead which felt awkward at first because he was shorter than me in my heels.. I quickly fell in my female role and as he placed his right hand on my lower back and embraced my right hand with his left hand near our chests. I placed my left hand on his right shoulder as we began to slowly turn and drift to the ballad.

It was nice to be held by a man, but I felt no attraction to him. I was using him to make Drake jealous. Oh what a conniving woman I was beginning to be and I loved it.

Towards the end of the song I caught Drake’s eyes. He seemed to be looking rather perturbed with his dance partner who appeared to be talking a mile a minute while chomping on a piece of gum.

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